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Jamaica

$100+ Cheap flights from Chicago (CHI) to Jamaica

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MBJ
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Chicago to Jamaica

Cheapest flights from Chicago to Jamaica
Explore the most affordable flight options available from Chicago to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This CheapOair deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:41 pm
ORD
-
KIN
1 stop14h 19m
Spirit Airlines
Thu 3/1912:17 pm
KIN
-
ORD
1 stop7h 29m
Spirit Airlines
Deal found 1/26$358
This FlightHub deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/205:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Fri 2/271:00 pm
MBJ
-
ORD
1 stop7h 11m
Spirit Airlines
Deal found 1/28$365
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:16 pm
ORD
-
KIN
1 stop14h 44m
Spirit Airlines
Sun 3/1512:17 pm
KIN
-
ORD
1 stop23h 04m
Spirit Airlines
Deal found 1/27$365
This CheapOair deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:19 am
ORD
-
MBJ
2 stops24h 43m
Spirit Airlines
Fri 3/61:00 pm
MBJ
-
ORD
2 stops31h 47m
Spirit Airlines
Deal found 1/28$367
This CheapOair deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/18:43 pm
ORD
-
MBJ
1 stop14h 19m
Multiple Airlines
Sun 2/87:05 pm
MBJ
-
ORD
1 stop26h 05m
Multiple Airlines
Deal found 1/27$368
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/204:42 pm
ORD
-
MBJ
2 stops18h 20m
Multiple Airlines
Fri 2/271:00 pm
MBJ
-
ORD
1 stop7h 11m
Multiple Airlines
Deal found 1/28$369
This CheapOair deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/158:41 pm
ORD
-
KIN
1 stop14h 19m
Spirit Airlines
Sun 3/2212:17 pm
KIN
-
ORD
1 stop23h 04m
Spirit Airlines
Deal found 1/28$369
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/281:00 pm
MBJ
-
ORD
2 stops12h 40m
Spirit Airlines
Deal found 1/27$370
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:51 pm
ORD
-
MBJ
2 stops39h 33m
Multiple Airlines
Thu 3/51:00 pm
MBJ
-
ORD
1 stop11h 05m
Multiple Airlines
Deal found 1/27$371
This Orbitz deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:00 pm
ORD
-
MBJ
1 stop21h 20m
Multiple Airlines
Sat 4/2512:00 pm
MBJ
-
ORD
1 stop7h 48m
Multiple Airlines
Deal found 1/27$372
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:51 pm
ORD
-
MBJ
2 stops16h 11m
Multiple Airlines
Sat 2/2812:40 pm
MBJ
-
ORD
1 stop10h 59m
Multiple Airlines
Deal found 1/27$373
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/85:01 pm
MDW
-
MBJ
2 stops18h 01m
Multiple Airlines
Thu 2/123:08 pm
MBJ
-
MDW
1 stop8h 26m
Multiple Airlines
Deal found 1/28$373

Find flight deals from Chicago to Jamaica

Keep the following information in mind while searching for Chicago to Jamaica flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(CheapOair)

One-way from

$100
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$529

Good round-trip deal

$480 or less

Good one-way deal

$248 or less
Provider with most accurate pricing for Chicago (CHI)-Montego Bay Sangster Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Montego Bay Sangster Intl flights.
Search Deals
From Chicago (CHI) to Jamaica
Search Deals
One-way flight from Chicago (CHI) to Jamaica
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Jamaica.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Jamaica.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Jamaica that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
Use the filters below to find and compare flights from Chicago to Jamaica that are best for you.

Fly from

Chicago

Fly to

Jamaica

Route

Depart

Return

Price

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 3/12

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Thu 3/19

12:17 pm-7:46 pm

1 stop7h 29m

$362

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/25

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Thu 2/26

3:25 pm-9:41 am

2 stops19h 16m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/23

2:05 pm-12:32 pm

2 stops21h 27m

Montego Bay Sangster Intl

Fri 2/27

2:00 pm-9:41 am

2 stops20h 41m

$381

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/18

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Wed 3/25

1:48 pm-6:13 pm

Nonstop4h 25m

$382

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/11

8:42 am-12:46 pm

Nonstop4h 04m

Montego Bay Sangster Intl

Sat 3/14

1:48 pm-6:13 pm

Nonstop4h 25m

$387

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Mon 3/16

12:17 pm-10:36 am

1 stop22h 19m

$388

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Tue 3/17

12:17 pm-10:36 am

1 stop22h 19m

$388

ChicagoMontego Bay

MDW - MBJ

MDWMBJ

Chicago Midway

Sun 3/1

6:40 am-2:10 pm

1 stop6h 30m

Montego Bay Sangster Intl

Thu 3/5

2:00 pm-11:35 pm

1 stop10h 35m

$392

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Wed 3/11

6:36 pm-11:00 am

1 stop16h 24m

Kingston Norman Manley

Thu 3/19

12:17 pm-7:46 pm

1 stop7h 29m

$394

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 3/12

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Wed 3/18

12:17 pm-7:46 pm

1 stop7h 29m

$396

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Jamaica

What is the cheapest month to book a flight from Chicago to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $96). Flying from Chicago to Jamaica in March is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to JM?

Find hourly flight availability from Chicago to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

When flying from Chicago to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Jamaica. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Chicago to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,393 reviews
Southwest
8.0
Very good
4,267 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Jamaica?

    A quick flight from Chicago to Jamaica can take about 4h 04m. Spirit Airlines provides one of the quickest options available for as low as $382. There are 1724 mi between Chicago and Jamaica. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Jamaica one-way?

    One-way options have recently been found by users for as low as $98 on Spirit Airlines. Other airlines that offer cheap prices include United Airlines from $157 and American Airlines from $164 one-way.

  • What are the most popular routes from Chicago to Jamaica?

    The most popular flight routes from Chicago to Jamaica are Chicago O'Hare Intl - Montego Bay Sangster Intl, Chicago Midway - Montego Bay Sangster Intl and Chicago O'Hare Intl - Kingston Norman Manley.

  • What are the cheapest flights from Chicago to Jamaica?

    On average you can expect to pay $410 for a flight from Chicago to Jamaica. The cheapest flight overall is $170 while the most popular route, (Chicago O'Hare Intl - Montego Bay Sangster Intl) is currently priced at $261.

  • Can I find deals for flights from Chicago to Jamaica that include hotel bookings?

    Yes. In addition to deals on Chicago to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Jamaica.

  • Can I find deals for business class flights from Chicago to Jamaica?

    Yes. Cheapflights offers flight deals from Chicago to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Jamaica (average of $96). Flying from Chicago to Jamaica in March is currently the most expensive (average of $405). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Providenciales flights
Midway to Punta Cana flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
St. Louis to Punta Cana flights
Midway to Nassau flights
Midway to Oranjestad flights
O'Hare Intl to Castries flights
Midway to Montego Bay flights
Midway to Saint Thomas Island flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Christiansted flights
Midway to Providenciales flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to St. John's flights
St. Louis to Oranjestad flights
St. Louis to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to Aguadilla flights
Midway to Santo Domingo flights
Midway to Simpson Bay flights
Midway to George Town flights
O'Hare Intl to Road Town flights
St. Louis to Kingston flights
O'Hare Intl to Kingston flights
St. Louis to Montego Bay flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Georgetown flights
St. Louis to Castries flights
O'Hare Intl to Santiago de los Caballeros flights
St. Louis to Simpson Bay flights
O'Hare Intl to St. George's flights
St. Louis to Providenciales flights
St. Louis to George Town flights
O'Hare Intl to Marsh Harbour flights
Peoria to Luis Munoz Marin Intl flights
O'Hare Intl to Freeport flights
Moline to Punta Cana flights
Moline to Luis Munoz Marin Intl flights
O'Hare Intl to The Valley flights
O'Hare Intl to Port of Spain flights

Top 6 airlines flying from Chicago to Jamaica

Discover the top 6 airlines that operate flights from Chicago to Jamaica. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$434FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$662FlexibilityNo cancel feeOn-time62%
DeltaCheapest$178Average$607FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$356Average$595FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$419Average$666FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$531Average$724FlexibilityNo cancel feeOn-time63%

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